The Column
Opinions, design details, and engineering lessons from the builders of trained.chat.
Why We Refused to Add Long-Term Memory to Our Default Agent Plan
Adding endless conversation history sounds great in startup pitch decks, but in production, it creates massive hallucination loops and spikes API costs. Here is the context architecture we built instead.
We Rebuilt Our Retrieval Pipeline Three Times. Here is What Actually Worked.
After auditing thousands of failed RAG queries, we threw out the standard tutorials. A detailed breakdown of parent-child overlaps and semantic node splitting.
Why AI Should Never Call Your Outbound APIs Without Permission
How giving agents raw tool-calling powers backfired, and the design pattern we built to request human confirmation for sensitive billing webhooks.
The Day Our AI Started Hallucinating and How We Fixed It in 4 Hours
An open postmortem on a bad prompts deployment, the debugging tools we used, and why we rebuilt our playground compare mode.
Founder's Notes
Lessons, mistakes, strategy, and architecture decisions from building in the open.
Engineering
Retrieval systems, infrastructure, AI performance, and production reliability.
Product Decisions
Why features shipped, why others were removed, and the trade-offs behind them.
Why AI Should Never Call Your Outbound APIs Without Permission
How giving agents raw tool-calling powers backfired, and the design pattern we built to request human confirmation for sensitive billing webhooks.
How We Qualified 100 Website Visitors Without a Single Sales Representative
Why generic lead gen chatbots annoy visitors, and how we designed custom interactive form cards that actually convert.
Customer Success
Support, onboarding, retention, conversation quality, and human handoff in production.
When Should AI Say 'I Don't Know'? Designing the Perfect Handoff Threshold
Too early, and you lose deflection. Too late, and you alienate customers. The exact mathematical scoring model we use to hand off active conversations.
Why Most AI Chatbots Fail 30 Days After Launch (And How to Avoid It)
A checklist of the data mismatches, prompt drifts, and compliance gaps that kill company agents once they touch live production traffic.
Design
Interface, motion, typography, and systems.
